


First Time

by Draquete



Category: Supernatural
Genre: Anal Fingering, Blindfolds, Bottom Dean, First Time, M/M, Rimming, Sam is fifteem, Top Sam, for a weekly challenge I'm making on tumblr so we can have more bottom dean fics
Language: English
Status: Completed
Published: 2017-01-24
Updated: 2017-01-24
Packaged: 2018-09-19 18:28:29
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,230
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9454976
Author URL: https://archiveofourown.org/users/Draquete/pseuds/Draquete
Summary: Sam and Dean's first time.





	

**Author's Note:**

> I started a weekly challenge to promote bottom!dean/jensen in the ships wincest and j2 on tumblr (at bottomdeansheaven) and the first prompt was first time. Since it's Dean's birthday, I wrote this. Hope you enjoy! (Also, if you're interested in participating, do it! Go to bottomdeansheaven on tumblr and participate!)

The first time they had kissed, it was on July 4th and Sam had been only thirteen years old. After that, Dean got so grossed out with himself, because it felt like he was taking advantage of his little brother, that he told Sam they couldn’t do it again.

It didn’t mean Sam stopped trying. In fact, it only made Sam more determined.

After a few months, Dean said that they could hold hands and cuddle and go to dates together, but they wouldn’t do anything sexual, including kissing. Sam pouted and whined and gave his best sad puppy look, but Dean wouldn’t corrupt his brother like this.

A year later, Dean conceded a kiss on Sam’s birthday, and then another on the fourth of July again, and then again on Thanksgiving and yet another on Christmas. On New Year’s Eve, when it struck midnight, Dean kissed Sam without his brother even asking for it. That day, they also had a proper making out session, but Dean stopped when things started getting a bit heated.

When Sam turned fifteen and couldn’t hold his urges anymore, he begged Dean for them to do _anything_. Even a handjob would be okay. He was just tired of jerking off three – or more – times a day when he had a brother – and boyfriend – that could easily help him out.

Dean conceded and he jerked Sam off, but he was still hesitant in letting Sam touch him. Dean wanted it, of course he wanted it, so damn badly, but Dean was still Sam’s big brother and responsible to keep his little brother’s innocence intact. And so far he had been failing miserably.

Later that year, Dean sucked Sam off and then had Sam do the same to him. And so, now they often jerked himself off or blew each other, but due to Dean’s worries, they never got completely naked, too afraid to be tempted to do things he might regret later.

On his twentieth birthday, though, Sam asked if he could give Dean a proper birthday gift. Well, a proper sexual gift. Dean hesitated, as always, but Sam had already bought him pie and was making sure Dean had a wonderful day. So he accepted.

Dean took out all his clothes and lied down on the bed, waiting. Dad was on a hunting trip and wouldn’t be back for at least another month, so he didn’t need to worry about his dad entering on them. Sam had left to buy something, so Dean tried to relax on his bed as much as he could. He was almost dozing off when Sam finally got back.

“Whatcha got?” Dean asked, propping himself on his elbows and he noticed Sam stood there in silence for a moment just to appreciate Dean’s body. Dean blushed, but he would deny it if Sam brought it up.

“Stuff.” Sam said cryptically and Dean only frowned, but then Sam smirked and dropped the bag on the floor by the bed. “Can I blindfold you?” Dean blushed even more at the idea.

“Aren’t we kinky?” He said in a hoarse voice, but then he nodded. “Okay. Why not?” Sam smiled brightly and he walked to the closet and fumbled with some things inside it for a moment before coming back with a tie. Dean swallowed dry but closed his eyes as Sam tied the tie above his eyes. “What now?”

“Now you just lie back, relax and let me take care of you.” Dean’s breath hitched at the prospect, but he did as he was told.

A moment later, Sam was kissing his lips. Relaxing even more, Dean kissed back, bringing his hands to Sam’s face, cupping his cheeks lovingly. They kissed for the longest of time until Sam started kissing down his neck and Dean could only turn his head to the opposite direction and give Sam even more space to kiss and bite at his neck.

Dean felt like Sam was fumbling with something as he sucked marks on his neck, but he was too busy groaning and relishing in the feeling to care what his brother was doing. A moment later, though, Sam lied down on top of Dean and Dean noticed Sam was completely naked, his cock hard and leaking against his own.

Sam took that moment to start kissing down Dean’s collarbone and chest, spending some time in each of Dean’s nipples, licking and sucking them like his life depended on it, making Dean writhe and squirm underneath him. Sam then continued his journey down Dean’s body, licking his abs before dipping his tongue inside Dean’s navel, which prompted a surprised yelp from Dean, hands going desperately to Sam’s head.

Sam just chuckled before starting to lick Dean’s shaft. He was teasing him, Dean noticed, and perhaps that was the reason why he had wanted Dean blindfolded in the first place. Sam’s hands went to Dean’s thighs, squeezed it for a moment before he tugged them enough so his legs were open and Sam was nestled in between them, tongue still working on his cock.

And with that, Sam finally put the cock in his mouth, sucking at the head, just like he knew Dean liked, and Dean moaned, hands still on Sam’s hair, but not tugging or pushing, just holding to have something to do with his hands. Sam continued sucking down his cock, but once it hit the back of his throat, he withdrew and started licking the length again, making Dean whine at the loss of that glorious mouth around his aching cock.

However, Sam made up for it by sucking Dean’s balls in his mouth, licking at them like they were a treat. Dean let go of Sam’s hair to hold on the sheets of the bed and unconsciously brought a leg up, giving Sam more space. Sam, though, continued licking down and down and Dean tensed up when Sam’s tongue found the rim of his hole.

“Sam?” Dean asked in a confused and desperate voice.

“Just relax, Dean. It’s your birthday, Dean, _enjoy_.” Dean swallowed dry once more before trying to calm himself down. They hadn’t done this before. They hadn’t touched each other’s holes yet and Dean had never even tried to touch himself there before, so this was all new. But Sam’s tongue felt so good that he chose to let Sam do whatever it was he was doing.

Sam’s licks were quick at first, but then he started forcing the ring of muscle with his tongue and breaching his brother’s entrance with his tongue. And soon he was fucking Dean with his tongue and Dean was moaning and panting like a cheap whore. He was sweating and his heart was beating so fast he thought he was going to explode. Even though this wasn’t Dean’s first time having sex, this was definitely the first time he felt anything like that.

After a while, Sam stopped again and Dean whined once more, needing more of that mouth on his hole, licking and fucking him. He tried calling for his brother again, but Sam just kept a hand on his thigh for a while before completely letting go. Dean held his breath, curious as to what Sam was doing, or if this was yet another attempt at teasing him, although he couldn’t understand why.

Dean only understood Sam’s motives when a finger entered him. Out of nowhere. It took him by surprise and he gasped, not used to the feeling, but thankful this wasn’t bad. Actually, it was pretty good, mainly when Sam started moving the finger in and out of him.

“Sammy…” He moaned, and he tried to find his brother with a hand, but couldn’t find him. Sam, however, took his hand and intertwined their fingers and he continued fingering Dean with the other hand.

“Do you like it, Dean?” Dean bit his lower lip and nodded, blushing slightly. God, and to think that he was thinking about waiting until Sam was eighteen for them to have sex for the first time. But this was clearly going one way and Dean didn’t want anything different. “I’mma add a second finger, okay?” Dean nodded once more and then Sam was fingering him with two fingers.

In the beginning, Sam only moved his fingers in and out, but when he noticed Dean undulating his hips wantonly, Sam decided Dean was ready for more. He started scissoring Dean as he finger fucked him and Dean was moaning and writhing and couldn’t stop calling Sam.

Another few minutes passed by with only two fingers, but when Dean was loose enough, Sam added a third finger and he already started stretching him, scissoring him with every movement of his hand. If Dean could think properly, he’d probably wonder where Sam learned how to do all that. Now, however, the only thing going through his mind was ‘more’.

It was only when Dean started to beg, his cock already leaking pre cum profusely, that Sam took mercy on him.

“Shh, Dean. It’s okay. I’m going to fuck you now.” Dean nodded dumbly at Sam’s words, wanting it so badly. Which was why he was surprised when Sam took off the tie from his eyes.

They stared at each other for a moment before Sam smiled and kissed him. Dean’s hands shot to Sam’s face and they kissed passionately, and in that moment, Dean knew he had failed to keep his brother a virgin, mainly since he was an adult himself. But that didn’t matter anymore. Sam was his and he was Dean’s, so what was the problem?

“I love you, Dean.” Sam said once they broke the kiss and then he started fumbling with the lube, spreading it all over his hard cock and Dean could just look and wait. Fuck, this was going to happen.

The first push inside made Dean’s ass twitch around Sam, but he kept looking at Sam’s eyes and calmed himself down, relaxing once more. And then Sam slid inside easily and they both moaned loudly.

“Fuck, Dean, you feel so good. It’s so… hot and tight. Fuck.” Sam had completely stopped once he was inside, and Dean knew it was because he was about to blow his load and needed a moment. Dean had to also take a moment. Not because he was about to cum, but because he had never thought he would enjoy a dick up his ass so much.

It got even better when Sam started moving. Slowly at first, but once Sam quickened his pace, Dean yelled when he felt the most blissed feeling coming from within him. Sam smiled and tried again, and every time he bottomed out, he hit the same spot inside Dean that would make him roll his eyes and moaned and beg.

“Sammy, oh fuck. Fuck, faster, Sammy.” He begged, and Sam moaned, nodding as he started to move even faster. He took Dean’s legs, changing their positions just enough to go harder and faster and Dean was dumbstruck at how good Sam was at this. Sure, he didn’t have anything to compare to, but he was fucking blissed out. “Wanna cum. Sammy, wanna cum.” Dean breathlessly said, a hand going to his own dick to help him cum already, but Sam slapped the hand away.

“No, Dean. Try to come on my cock.” Dean whined, and it must have been clear on his face how he didn’t think that was possible, because Sam continued: “I’ll blow you if I come before you do, but try, Dean. Fuck, that would be so hot. Don’t you think? Fuck.”

Dean had to agree that it would be so fucking hot, and the way Sam said the words and the way he was clearly turned on by the idea only made Dean even more aroused. His orgasm was so damn close, he could almost taste it, but he still needed more, a little push.

“Sammy…” Dean gasped his brother’s name, tugging him. Sam put Dean’s legs on his shoulders before lying down on Dean, his legs in between them, but this new position made all the difference. It was so much more intense, Sam was even deeper within him and without even being able to stop himself, he came almost violently in between them.

“So – fucking – hot.” Sam said each word at a new thrust and by the end of it he was coming too. They remained that way for a while, but then Sam pulled out and let Dean’s leg fall back to the bed. He then laid on the bed by Dean’s side, half on top of him. “Happy birthday, Dean.”

“Fuck, thanks, Sammy.” Dean said and then chuckled, eyes closed for a moment as he tried to get his breath back. When he turned to look at his brother, Sam had this satisfied, proud smile on his face, which made Dean smile as well. “What?”

“I’m glad you let me fuck you. We can do it more often now.” Sam stopped for a moment and frowned. “You’re not going to freak out, are you?”

“Nah. I think it was about time it happened, actually.” Dean said, and Sam smiled so brightly that Dean was sure he said the right thing. “Love you too, baby brother. Thank you. It’s been an awesome birthday.” Sam just smiled and kissed him again.


End file.
